Potassium Carbonate → tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate

HRID 1157181Notes

Reaction equation

HRID 1157181 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>O1CCOCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 16217943tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Potassium carbonate (1.7 g, 12.31 mmol) was added to a solution of 2-Chloro-5-nitropyridine (1.33 g, 8.38 mmol) and piperazine-1-carboxylic acid tert-butyl ester (1.57 g, 8.42 mmol) in dioxane (10 ml) then stirred at reflux for 4 hours. The reaction was cooled, and solvent evaporated. The residue was extracted with MeCl2 (100 ml) washed with H2O (50 ml), separated organic layer washed with brine (50 ml) dried over MgSO4, filtered and solvent evaporated yielding a residue which chromatographed on silica gel eluting with 10% v/v EtOAc/hexanes yielding desired product as a pale yellow solid (2.3 g, 88%)

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction was cooled
  3. customsolvent evaporated
  4. extractionThe residue was extracted with MeCl2 (100 ml)
  5. washwashed with H2O (50 ml)
  6. customseparated organic layer
  7. washwashed with brine (50 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customsolvent evaporated
  11. customyielding a residue which
  12. customchromatographed on silica gel eluting with 10% v/v EtOAc/hexanes yielding desired product as a pale yellow solid (2.3 g, 88%)

Sources & evidence

ORD record
ord-29e2cd2e46764ec5b6c103f82f906ec9
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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